1.01 mil TP here, and I lost my first squad against the deck-boss once (not a single special triggered on the second round of the battle, and it's a trigger-team!) and the whaleship against the ancient pest once (again, not a single skill trigger except 1 Grand Slash at the start of the map when the boss was about to run anyway, while the boss got several critical hits).
Generally, I finished the map with 30%-60% health left on the whale ship. Haven't tried the map again with Fritillaria's new earrings yet, but I don't expect major differences, just the deck-boss might be slightly easier.